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2-bromo-4-N, N-dimethylaminoimidazole and preparation method thereof

A technology of dimethylaminoimidazole and imidazole bromide, which is applied in organic chemistry and other fields, can solve problems such as waste acid pollution, and achieve mild reaction and easy operation

Active Publication Date: 2022-04-01
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on the preparation of aminoimidazole compounds often uses the nitrification reduction method, which involves strong acid and produces waste acid pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The 2-bromo-4-N of the present embodiment, the preparation method of N-dimethylaminoimidazole is as follows:

[0018] Take a 100ml single-mouth bottle, add 19g of 4-nitro-2-bromoimidazole, and add 16.58ml (11,27g) of dimethylamine aqueous solution with a mass concentration of 40%, stir and dissolve, react at 25°C for 10h, and rotate to evaporate Part of the aqueous solution was removed, and pale yellow crystals were precipitated, which were filtered and washed with water to obtain 14.59 g of a yellow solid, with a yield of 76%.

[0019] MS: m / z: [M+1]: 189.9.

[0020] 1 H NMR (400 MHz, DMSO-d6): 8.31 (br, 1H), 7.58 (s, 1H), 2.57-2.51 (d, 6H)

[0021] Elemental Analysis C 5 h 8 BrN 3 : C, 31.60; H, 4.24; Br, 42.05

[0022] Measured values: C, 31.48; H, 4.26; Br, 42.24.

Embodiment 2

[0024] The 2-bromo-4-N of the present embodiment, the preparation method of N-dimethylaminoimidazole is as follows:

[0025] Take a 250ml single-mouth bottle, add 19g of 4-nitro-2-bromoimidazole, and add 82.88ml (56.36g) of dimethylamine aqueous solution with a mass concentration of 40%, stir and dissolve, react at 25°C for 10h, and remove by rotary evaporation Part of the aqueous solution precipitated pale yellow crystals, which were filtered and washed with water to obtain 16.62 g of a yellow solid with a yield of 87%.

Embodiment 3

[0027] The 2-bromo-4-N of the present embodiment, the preparation method of N-dimethylaminoimidazole is as follows:

[0028] Take a 250ml one-mouth bottle, add 19g of 4-nitro-2-bromoimidazole, and add 165.74ml (112.7g) of dimethylamine aqueous solution with a mass concentration of 40%, stir and dissolve, react at 25°C for 10h, and remove by rotary evaporation Part of the aqueous solution precipitated pale yellow crystals, which were filtered and washed with water to obtain 17.99 g of a yellow solid with a yield of 94%.

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Abstract

The invention discloses 2-bromo-4-N, N-dimethylamino imidazole and a preparation method thereof.The preparation method comprises the steps that 4-nitro-2-brominated imidazole is dissolved in a dimethylamine water solution, and a reaction is conducted for 6-10 h under the room temperature condition to obtain a mixed solution; carrying out rotary evaporation on the mixed solution to remove part of water, separating out faint yellow crystals, and carrying out post-treatment to obtain 2-bromo-4-N, N-dimethylaminoimidazole; the specific reaction equation is shown in the specification. The structure of the 2-bromo-4-N, N-dimethylaminoimidazole is confirmed through nuclear magnetic hydrogen spectrum, carbon spectrum, mass spectrum and elemental analysis, according to the preparation method of the 2-bromo-4-N, N-dimethylaminoimidazole, the reaction only needs to be carried out in water at room temperature, and a pure product can be obtained only through suction filtration after the reaction is finished. The method is simple to operate, mild in reaction and suitable for large-scale preparation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 2-bromo-4-N,N-dimethylaminoimidazole and a preparation method thereof. Background technique [0002] Aminoimidazole compounds are an important class of heterocyclic compounds, which are often used as drug molecular fragments. It has a variety of pharmacological activities, such as the function of inhibiting cell proliferation activity. Many current inhibitors contain aminoimidazole structures (Journal of Chinese Pharmaceutical Sciences, 2017, 26(09): 650-659; Synthetic Chemistry, 2018 ,26(09):637-646), so the research on aminoimidazole compounds has good pharmaceutical research value. However, the current research on the preparation of aminoimidazole compounds often uses the nitrification reduction method, which involves strong acid and produces waste acid pollution. The present invention adopts the substitution method, and the reaction only needs to be car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/88
Inventor 闫福丰靳清贤陈嘉璐张会均王旭哲
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY